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Named Reactions in Organic Synthesis
Pericyclic and photochemical reactions
Other featured pericyclic reactions:
Featured photochemical reactions:
In 1964 the Swiss chemist Albert Eschenmoser reported that allylic or benzylic alcohols heated in the presence of N,N-dimethylacetamide dimethyl acetal in xylenes underwent a form of Claisen rearrangement. This generated a γ,δ-unsaturated amide with a high level of stereospecificity, and today this transformation has become known as the Eschenmoser - Claisen rearrangement.
This rearrangement typically occurs at lower temperatures, between 100-150 degrees centigrade, than other variants such as the Claisen rearrangement itself and is more (E) - selective.
During the first total synthesis of (±)-Stenine by D.J.Hart and colleagues, one of the key steps was an Eschenmoser - Claisen rearrangement that afforded a key amide intermediate in 93% yield.
Mechanism of the Eschenmoser-Claisen rearrangement:
Other reaction categories:
Some relevant Alfa Aesar products for the Eschenmoser-Claisen rearrangement:N,N-Dimethylacetamide dimethyl acetal, tech. 90%, stab with 5-10% methanol
Xylenes, mixed, 97+%
Xylenes, ACS, 98.5+% (Assay, isomers plus ethylbenzene
We have many allylic and benzylic alcohols in our portfolio.